Method for the production of a halogenated alkene by catalyzed dehydrohalogenation of a halogenated alkane

Patent metadata

Field	Value
Publication number	US-11358918-B2
Application number	US-201916981984-A
Country	US
Kind code	B2
Filing date	Apr 2, 2019
Priority date	Apr 3, 2018
Publication date	Jun 14, 2022
Grant date	Jun 14, 2022

Abstract

The present invention provides methods for the preparation of halogenated alkenes from halogenated alkanes using a homogeneous catalyst.

First claim

What is claimed is:

1. A process for preparing halogenated alkenes, the process comprising:
a) preparing a liquid reaction mixture, wherein the reaction mixture comprises at least one halogenated alkane and at least one homogeneous catalyst comprising at least one metal salt, wherein the concentration of the homogeneous catalyst in the reaction mixture is 50 ppm or less; and
b) forming, from a reaction of the reaction mixture, at least one halogenated alkene, wherein the reaction is carried out at a temperature of at least 150° C.

2. The process of claim 1 , wherein the concentration of the homogeneous catalyst in the reaction mixture is 8 ppm or less.

3. The process of claim 1 , wherein the concentration of the homogeneous catalyst in the reaction mixture is 8 ppm to 50 ppm.

4. The process of claim 1 , wherein the concentration of the homogeneous catalyst in the reaction mixture is 10 ppm or less.

5. The process of claim 4 , wherein the homogeneous catalyst comprises one or more of FeCl 3 or GaCl 3 .

6. The process of claim 4 , wherein the homogeneous catalyst comprises FeCl 3 .

7. The process of claim 1 , wherein the concentration of the homogeneous catalyst in the reaction mixture is 30 ppm or less.

8. The process of claim 1 , wherein the at least one metal salt is selected from the group of an aluminum salt, a bismuth salt, a chromium salt, a cobalt salt, a copper salt, a gallium salt, a gold salt, an indium salt, an iron salt, a lead salt, a magnesium salt, a manganese salt, a mercury salt, a nickel salt, a platinum salt, a palladium salt, a rhodium salt, a samarium salt, a scandium salt, a silver salt, a titanium salt, a tin salt, a zinc salt, a zirconium salt, and combinations thereof.

9. The process of claim 1 , wherein the reaction is carried out at a pressure of at least 0 psig.

10. The process of claim 1 , wherein the conversion of the at least one halogenated alkane is greater than 50%.

11. The process of claim 1 , wherein the conversion of the at least one halogenated alkane is greater than 70%.

12. The process of claim 1 , wherein the selectivity to the at least one halogenated alkene is greater than 90%.

13. The process of claim 1 , wherein the selectivity to the at least one halogenated alkene is greater than 99%.

14. The process of claim 1 , wherein the halogenated alkane is a chlorinated alkane.

15. The process of claim 12 , wherein the chlorinated alkane is one or more members selected from the group of 1,1,1,3-tetrachloropropane (250FB), 1,1,1,2,3-pentachloropropane (240DB), 1,1,1,3,3-pentachloropropane (240FA).

16. The process of claim 1 , wherein the halogenated alkene is a chlorinated alkene.

17. The process of claim 16 , wherein the chlorinated alkene comprises between 2 and 6 carbon atoms and one less chlorine atom as compared to the chlorinated alkane.

18. The process of claim 16 , wherein the chlorinated alkene is a chlorinated propene.

19. The process of claim 1 , wherein the liquid reaction is anhydrous.

20. The process of claim 1 , wherein preparing the liquid reaction mixture comprises adding the homogeneous catalyst dissolved in a solvent.

Assignees

• Blue Cube Ip Llc

Inventors

• Tirtowidjojo Max
• Kokott Manfred
• Sell Marc
• Myers John D
• Peters Anja

Classifications

• C07C17/357 Primary

  by dehydrogenation · CPC title

• C07C17/25 Primary

  by splitting-off hydrogen halides from halogenated hydrocarbons · CPC title